Lithium Hydroxide → HCID 9891103, compound

HRID 378143Notes

Reaction equation

FC(F)(F)C(O)=O.[C:8]1([CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:20]=[C:21]([C:25]([NH:27][CH2:28][C:29]([NH:31][CH:32]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)[CH2:33][C:34]([O:36]CC)=[O:35])=[O:30])=[O:26])[CH:22]=[CH:23][CH:24]=2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Li+].FC(F)(F)C(O)=O>O.C(#N)C>[C:8]1([CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:20]=[C:21]([C:25]([NH:27][CH2:28][C:29]([NH:31][CH:32]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)[CH2:33][C:34]([OH:36])=[O:35])=[O:30])=[O:26])[CH:22]=[CH:23][CH:24]=2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 105 (400 mg, 0.094 mmol) was dissolved in water/acetonitrile (1:1), followed by the addition of lithium hydroxide (100 mg, 0.4 mmol). The reaction mixture was stirred at 25° C., and monitored by HPLC. After complete hydrolysis (1-2 hours) trifluoroacetic acid was added until pH=2. The product was purified by reverse phase chromatography (water/acetonitrile) to result in a white solid (200 mg). MS and 1H-NMR were consistent with the proposed structure.

Workup

additionwas added until pH=2
customThe product was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record: ord-bcad13b7cb074157942d11c6afcb7dc3
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028223

Reaction notes

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